Reader Request: Over-dressing and Under-dressing

Eternal*Voyageur said:

I´d love to know your thoughts about over-dressing: like wearing something nice to a supermarket and something really extravagant to a casual occasion. I don’t mean expensive pieces, but just something elaborate and pretty. Do you think overdressing is pathetic and a sign of a boring life, or do you think it´s the rest of the people under-dressing that´s the problem?

First of all, I don’t believe that ANY kind of dressing is pathetic. Every woman has her reasons for choosing her clothing, and assuming that I could accurately gauge those reasons by looking at her is pure foolishness. That goes for over-dressing, under-dressing, dressing differently from peers, dressing impractically, dressing in ways that I cannot personally fathom … you name it. I am continually fascinated by the choices of others, but do my best to reserve judgment.

As for the specific questions of over- and under-dressing, let’s start on the casual side of the coin, shall we? I’ve heard many style experts claim that casual clothing culture has ruined our society. RUINED it! And while it makes me a bit sad to attend the opera wearing my best dresses and heels while my fellow audience members listen, rapt, in their sweatshirts and jeans, I don’t consider such shifts in style to signal deteriorating human morals. Life has gotten harder, faster, more overwhelming, and scarier as the years have worn on. If people elect to wear their comfies at all times as a means of keeping an even keel, feeling happy and secure, or for any other reason, who am I to judge?

As for over-dressing, I’m a fan. I wear dresses on Casual Friday, heels to the grocery store, statement necklaces for dinner at Wendy’s. For much of my career, I was overdressed ALL THE TIME. Which, I suppose, is directly related to the aforementioned casual clothing culture that has overtaken my country. But it’s also related to my unabashed love of clothing and style. I have absolutely no problem with people who dress down, but my personal preference is to dress up. And it delights me to see others who choose to dress up, regardless of context. Typical objections to over-dressing – it’s vain, it’s a sign of self-absorption, it makes others feel self-conscious – strike me as petty. If people want to wear ballgowns to the bowling alley as a means of self-expression, attention-seeking, or for any other reason, who am I to judge?

All that said, I prefer to have some sense of the level of formality before attending an event, meeting, or gathering. Although I respect the right to choice, I also acknowledge that fashion is social, that we project information about ourselves through our clothing choices, and that dressing well broadcasts self-respect outward to the observing world. Additionally being over- or under-dressed can attract negative attention in certain circles, creating uncomfortable social situations. Some people could care less about making waves, but personally, I err on the side of conformity of dress. When moving among strangers, I prefer to rely on my intelligence and personality to make waves for me.

Although certain situations ambush us, we can generally guess which outfits will make us appear over- or under-dressed. Taffeta dresses will look out of place at PTA meetings, sweatpants will seem odd at weddings. If you end up over- or under-dressed for any reason at all, my only advice is to own it. If you’re intentionally dressing outside the social norm, own it. Be confident and bold, flippant and carefree, and many will admire your strength. If you accidentally dress outside the social norm, own it. We’ve all been there, and laughing with others will demolish social barriers. Either way, you might as well embrace your position as sore thumb with good humor. Acting embarrassed and ashamed will simply prevent you from enjoying yourself, being yourself, and connecting with people who accept you no matter what you’re wearing.

Image courtesy Charline Tetiyevsky.

Originally posted 2011-03-24 06:23:44.

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79 Responses to “Reader Request: Over-dressing and Under-dressing”

  1. Casey

    I am with you in the perpetually over-dressed category. I LOVE wearing dresses, pumps and unabashedly feminine pieces. So usually this means I am more “formally dressed” (though I hesitate to use that phrase–just because people tend to view it negatively and as snobbish) in most situations. Date night out to the suburban movie theater with my husband? You’ll most likely find me in a pretty 60s day frock with kitten pumps and a swipe of pink lipstick. Sunday at church? I think I’d fit right in with the stylish older ladies who sport extravagant hats in a myriad of hues. Even seemingly mundane things like running to the grocery store I tend to “dress up” because it pleases ME. Which is why I do wear what I wear in the first place: it not only seems like a natural extension of my inner personality and viewpoint, but brings a smile to my face and gives me a moment of pleasure when picking out an outfit for the day. That being said, I do think there is something in choosing appropriate clothes for the context of the situation. A ballgown while going camping probably isn’t the most practical thing. Or a swimsuit and sarong to a formal wedding at a country club (unless that’s what the dress code specifies! ;). So in a way although I enjoy wearing things that may look more dressy to others, I always keep context in the back of my mind. Because ultimately if you’re dressed inappropriately, well, you’re just that.

    Just my $0.02! 😉

    ♥ Casey

    • Miranda

      I agree with Casey about context.
      There’s something to be said for dressing slightly above the mark and feeling good about it in some contexts.

      But context, context. It reminds me of a year or two ago, when my large-city immediate family gathered together to go to my rural-small-town-cousin’s wedding. My mother wanted to wear a full-length, emerald green silk gown with jewels — far more formal than the bride would or could ever afford to be herself. While I understand feeling good about being the nicest dressed in the room sometimes, there was something that just struck me as wrong here! (We did convince her to wear a more “appropriate” jersey day-to-evening dress instead.)

  2. Magatha May

    I’ve often found myself in a situation where I’m under and over dressed. My advice… always keep a few pairs of fab heels in the car and a few cardigans. hells can dress up the dreariest outfits – even sweats, and a cardi can tone down the most dressiest of dresses.

  3. Relatable Style

    “If you end up over- or under-dressed for any reason at all, my only advice is to own it.” YES, OH YES. I absolutely second that.

    But I have to admit, I personally find that easier to do when overdressed. Which kind of answers your other question: I definitely prefer to be overdressed and am rarely underdressed for any occasion. In my opinion: YAY! 🙂

    About too-casual clothing, I agree with you, too. I’ve read a lot of US fashion bloggers complaning about the amount of sweatpants they see in daily life. Maybe they are exaggerating to get the point across, I don’t know. It does not seem to run as rampant over here (for now), and I’m not one to judge anyone, but boy am I glad about that. I love to dress up (way up even, although I don’t have nearly enough occasions for that in my life 😉 ) and when I do that, my night is even more fun if I’m not the only one in glitz and glamour while everyone else in hanging out in jeans. Imagine my disappointment when I dressed up Bond girl style for a casino night (jacket required) and everyone was there in work attire: jeans and a blazer. Oh well. To each his own 🙂

    Relatable Style

  4. Carbon Girl

    This is a great post. I work in an uber-casual environment (I am an ecology grad student) and I always imagined all the pretty things I could wear when I got a real job. But I was getting real sick of t-shirts and jeans everyday, even though I always tried to wear my nice, not faded, well-fitting items. Over Christmas, I discovered your blog and that was it. I decided to no longer wait to dress how I wanted, that I would dress how I wanted right then and there. I now wear skirts or dresses 75% of the time and some button downs and blazers and accessories! It took a month for my colleagues to get used to it and stop making comments like “Wow you are dressed up, you must have a big meeting/teaching/presentation today.” Added bonus: I feel more confident dressing how I always wanted to.

    I am glad you don’t judge others for clothing choices but I cannot help it when I see some professors wearing ill-fitting jeans and faded tie-dyed t-shirts to work. To me that conveys a bad message to the world–one of a lack of respect for yourself and your profession. (I know, it is not right to judge.)

    • JennyDC

      I try not to judge, too – but I do. Just a little. I also get grumpy about uber-casual, because I think now it’s possibly to dress nicely and comfortably for not a ton of money. Sure, a jersey dress from Target won’t last as long as one from Theory (maybe!), but it looks nice and is comfy and should last at least a couple of years.

      But I am trying not to judge. I guess I would be less judgey if I didn’t think the judgement was even worse the other way – if you dress nicely you are a vain, shallow creature who can’t possibly take her work seriously or be an expert in anything besides appearance (although I actually am quite proud of how my ability to dress well has evolved!).

      I do agree that the “own it” advice is spot-on, and I am trying to adopt this attitude more fully.

  5. Stacey

    I’m not as confident as you are Sally, I generally don’t dress up all the time. I try to dress for what I think that most people will be wearing. With that said, I do not think it is appropriate to wear pjs to the grocery store. So I do believe that in America, we have become too casual. I also will not wear sweat pants in public. I love them to wear around the house and to work out in but I won’t wear them in public. Even if I had to stop at the store on my way to the gym, I make a conscious effort to make sure that they are not tight, leaving nothing for the imagination, as I have seen lately.

  6. Francesca

    Bravo, Sally! Love what you say about owning it, whether you’re under or over-dressed. In the end, it’s one’s personality & intelligence that will make a more lasting impact and can offset others’ impressions about your clothing choices. That said, I tend to overdress also, simply because as a SAHM who loves clothes, I have few opportunities to wear my nice stuff so I work it whenever I get the chance. Although always appropriate to my surroundings & aware of conforming to local mores, I do err on the side of more dressy/casual elegance/stylish/current fashion (whatever you want to call it). I don’t do it to get compliments (though they often come), I do it because I like to express personality thru color/style choices!

  7. Sara

    Oh, Sal, I love this post. I am also usually over-dressed, although I see it as “dressed.” I’ve found that when I try to “dress down” or blend in for whatever reason, I feel less like myself, like I’m trying to look like someone else… which I am. Your thoughts at the end, to just own it whether you’ve made the decision or made a mistake, whether you’re over or under dressed, are spot on and well said.

  8. Cynthia

    As you know, my outfits are pretty casual — lots of knitwear and nothing too structured or formal. But in my work environment, I sometimes feel “overdressed” just by virtue of making an effort at all. Combining clothes that look good together, wearing things that have a little deliberate ornamentation, or color or pattern for that matter, stands out. I’m a little worried that I may be seen as “underdressed” by people like our Dean while simultaneously seeming “overdressed” to my peers.

    I don’t think casual clothing culture is eroding society — but I think people wear casual, poorly-fitting clothing because that’s what you can get cheaply and in large quantities, and we are definitely fixated on cheap and in large quantities in America, and not on small collections of excellent things that fit perfectly.

  9. spuffyduds

    I’m more cautious about not drawing attention to myself with under- or overdressing if I’m attending an event that I feel “belongs” to someone in particular. Weddings belong to the couple, funerals belong to the family, high school band concerts belong to the performers, etc., and the attention should be on THEM and not on “that woman with the giant hat.”

    Grocery store? Wear your prom dress and combat boots and dance down the produce aisle, baby, it ain’t anybody else’s show.

  10. Danielle

    I’m always overdressed too. I always get the “well don’t you look fancy” comment. I just figure I like what I like and if I’m comfortable with it then so should everyone else…

    • Sal

      It never ceases to amaze me that “fancy” can come out sounding like an insult. I LOVE fancy! But it definitely rankles some people to see others dressing on a different level of fancy than they’ve deemed appropriate.

      • rb

        I get that too. I say, “THANK YOU!” delightedly, and move on. 🙂

  11. Reggie

    All I know is that I hate looking at people’s inner thighs in shortie shorts. It just makes me want to scream. I don’t care how meaty or bony your legs are. Its just too much for my poor little heart to take. Shortie shorts are too casual for any wear but the beach/pool or six flags to me and its only March and I’m already so tired of seeing them.

  12. Allison

    I overdressed for a work related event once – I felt GREAT… untill I walked in and saw everybody else, and then the comments started. I was less confident back in those days, and probably would handle differently now, but back then I wanted to just hide. Awkward.

  13. Kristen

    I dress how I feel and in clothes that I can chase a toddler in. On workdays, I prefer dressy pants, tsubo/clarks heels, a swingy cardigan or cute jacket with a scarf; on the weekends, it’s jeans, a cute shirt/swingy cardigan, and ballet flats or clarks wallabees. I think I look put together, not messy, and I have never owned sweatpants/shirts that I would wear out of the house. 🙂

  14. Mistie

    I tend to under-dress. I like my jeans and my t-shirts, although, I’m trying to play it up a little more. Growing up, I was a poor kid. My mom made a lot of my clothes (which was awesome), and the rest tended to be hand-me-downs. My two best friends were not poor and had extremely stylish mothers. When I was a teenager, my family was doing better financially, but dressing down had become a defense mechanism–fancy t-shirts? No thanks, I’m not worried about that stuff. I’m more worried about my grade point average. I’ve realized that a lot of my likes and dislikes in elementary and high school were in direct relation to the pressure I felt in our society to not be poor. That was the worst thing you could be. To admit that my family couldn’t afford all of the Barbie accessories was not an option, so I hated Barbie. Later, when my family couldn’t afford fancy prom dresses, I decided that I wasn’t concerned about style. I’m trying to explore my own personality and choices more, but I still feel best in a nice fitting pair of jeans and a quirky t-shirt from goodwill.

    • Mistie

      I forgot to mention that I love seeing people dressed fancy! A person who owns their style fabulously is like a treat for my eyes, so for all of you fancy dressers, keep it up!

  15. AW

    Oooh, good topic.

    I try to wear something that’s appropriate for the occasion, flatters me, but doesn’t necessarily make me the center of attention. I think I typically “overdress,” meaning that I’m almost always a step above khakis and a puffer vest, which is what 90% of the neighborhood wears. I do find myself laying off the ornamentation and accessories because I live in a very casual place.

    I don’t worry about what I wear to the grocery store, because it’s right across the street from my house, so it’s not like I have to make a special trip or get dressed *just* to get groceries. I’ve popped in there in everything from pool gear (covered up of course), workout sweats, and an evening gown with heels and a clutch.

  16. laura

    Fantastic Post! I am always overdressed. which has actually rubbed off on some of my friends. They say things like…”well i know you are going to be dressed up so i did too…” I love hearing that.

    I do think casual wear has overtaken WAY too many people. My main argument for overdressing is that i wear jeans and rubber boots to work all day long. When i go out, I play it up and wear fun party dresses, boots and accessories. overdressed to some makes me feel fantastic.

    • Carbon Girl

      I got that for my birthday dinner last week. Two of my friends dressed up because they knew I would be and that I would be happy to see them dressed up. Also, the woman I share an office with has started to dress up more now too, and I can’t help but thinking seeing me dress up each day rubbed off on her and gave her the confidence to pull it off too.

  17. T.

    As a stay-home mom, my main concern with dressing a little bit nicer for ordinary occasions, such as volunteering at school, or for school events, is that the other parents will think I am dressing up for such events because I have nothing else to dress up for. I need to stop worrying about what other people think. A month or so ago there was an evening school event, and I struggled with what to wear. I knew most people would be dressed in jeans, and I didn’t want to stand out, but I really really wanted to wear something a bit nicer. I put on the nicer outfit (dress, leggings, boots) and before I could chicken out and change my clothes, I got in the car and went. I felt great all night! I gave myself the courage to do it by thinking “Sally wouldn’t think twice about wearing this outfit to this event”, so thanks, Sal!

  18. zora

    i tend to dress pretty casual on most normal days, because im tired and dont have a lot of energy to do more than throw on some jeans. But when i see people in pretty dresses, or amazing outfits, even if it’s ‘overdressed’ for the situation, it makes me a little giddy! makes me smile a bit and a little jealous ;o) so, if you like to dress up fancy, keep doing it!! cause those of us that matter love it and are impressed, and if anyone is judging, screw ’em… ;o)

    • chelsea

      I agree completely. I love seeing people well dressed! It doesn’t make me uncomfortable or judge-y at all, so keep it up “fancy” dressers.

  19. Colleen

    I wear dresses 95% of the time to sit in a lab by myself analyzing brain scans :). Being in an environment where this is ok is important to me. At my interviews I definitely noted whether women in the departments wore heels, skirts, etc. or if it was all frumpy khakis and boxy blazers. At my last job I was reprimanded for being “too colorful” – I actually emailed you about it and you wrote such a nice reply. In that environment, women were expected to be either frumpy at worst or Ann Taylor catalog clones at best. Full makeup would get you looks. Where I am now is much less conservative and in a larger metro area, and it is such a better fit. People in my academic department have even suggested creating a “style award” just for me, which makes me feel so flattered – not to mention relieved! I’m always afraid of being dismissed or looked down upon for dressing on the eccentric side. Here the director of our department who is in his late 50s wears purple stretch jeans so that’s not an issue! It is very liberating to play with my style, wear bright eyeshadow, etc. I realize that I need to be in a place where weird is normal, if that makes sense.

    Oh, and I have never gotten negative reactions for overdressing and I think it’s because I dress for me first, others second. If I’m happy in my 50s party frock and crinoline, it doesn’t matter to me what someone in jeans thinks of my outfit.

    I also find that for whatever reason, I saw a lot more schlubbiness (sweats, PJ pants, disheveled hair) in Boston than I do in NYC. I guess NYC is just much more of a fashion forward city.

  20. Elizabeth

    My parents’ generation used to have a saying that if you weren’t sure what everyone would wear to an occasion, it would be better to err on the side of being a little under-dressed rather than over-dressed. But, they all dressed so nicely in every day life (and still do, judging by the well-groomed and beautiful older ladies at my father’s assisted living place) that a little too much formality could put them over the top. I’m not sure that that standard still applies in today’s world, where you’d practically have to go in your p.j.’s to something to be under-dressed. Maybe, we’d do better to err on the side of being just a little over-dressed and very nicely groomed. I think it’s a good point that we do all want to feel comfortable in our fast-paced world. I feel that way sometimes. There are times when I have good intentions of dressing a little more “formally”, but end up reaching for something comfy and casual. I also think it’s a good point that we should not judge people by what they wear, either way. As Jesus says in Matthew 6, we are all more important than what we wear. But, I do enjoy it when I see someone who is nicely and creatively dressed. It does seem to make the world a little more cheerful.

  21. Diana

    I’m with you – I am overdressed most of the time, and vastly prefer it to being underdressed. Despite the fact that I don’t wear makeup, high heels, or do my hair… To be fair, I work in a lab and just caring about clothes puts me squarely in the overdressed category. Here, most people are either of the schlumpy vendor tee + baggy jeans + sneakers school or the decent and clean but always the same school.

  22. Stacy

    I often tend to overdress, and I see no problem with that at all! By now my friends, family and coworkers are used to it. I love clothes and fashion and PRETTY. In our society it seems people don’t like to dress up anymore. I don’t understand why that is either. I guess I have romantic notions. I do dress in jeans when the situation warrants it, but I prefer skirts whenever possible.

    There was a funeral I was at a few years ago and one of the granddaughters of the man that had passed showed up looking like she just got finished feeding her horses and came straight from the barn. Her hair even was all messed up. Really?? How is that respectful in any way? *sigh* While I don’t think society is exactly deteoriating with the dressing down, I do think that it’s gone downhill a bit.

  23. ismay

    I agree wholeheartedly. I am often what others consider over-dressed – dresses and skirts in a very jeans+tshirt academic environment. But being from Europe, where people dress with more care, and thinking of more formal professional environments, I would be underdressed there… seeing how most of my pieces are inexpensive and colorful. So, its all context and expectation. I look upon it as a means of self-expression, fun, brightening uo a tedious or difficult day, and just making myself happy, and I do bemoan the lack of opportunities in our culture to really dress up…

  24. Apple A Day

    I too am a BIG fan of overdressing. Jeans and T-shirts are just boring. I love my beautiful clothes far too much to banish them to special occasions only. There are also some practical reasons to overdress:
    1) It can never hurt: Unless you are showing up to a fitness class in stilettos and a leather mini-skirt overdressing can be helpful. Case in point: In my job as a teacher, I’ve been better dressed than everybody who has ever interviewed me for a job. Far from being, “nerdy” I think it really set me apart and showed that I cared about getting a job. When you are young and inexperienced this can really work in your favorite.
    2) It just might brighten somebody’s day. I get a lot of smiles when I wear something pretty and unexpected. People like to see a brightly colored silk scarf on a dreary day or a pretty dress on an average day. It takes us out of the ordinary and spices life up a little, for you and for others. For more on my philosophy on work attire, check this out!

  25. Misty

    I too tend to dress on the dressy side of casual, its just my style and having a baby face i get asked if I’m 16 (I’m 26) when i wear an uber casual outfit. Don’t get me wrong, I love, love that I look younger then i am.. that will come in handy as time goes on, but you couldn’t pay me to go back to 16.Yikes! I personally make it a point in my daily life to tell any random person I see out and about with a super cute outfit, rocking their own style, or a unique piece in a totally unconventional way, and as soon as I complement them, they instantly light up, which in turn makes me feel great and the added bonus of style inspiration isn’t bad either. Us ladies need to stick together, if you see something you like… let them know.

  26. Emily

    I see A LOT of pajama pants and sweatpants in public. Gray sweats seem almost standard among middle-aged men here.

    Generally speaking, I try to look put-together, even if it is a jeans and t-shirt sort of day. Right now, I’m still in my pajamas (oh, the shame) and I’m not sure if I can bring myself to go out into the lobby to check my mail.

    A lot of my style is influenced by time I spent in Spain as a student. The biggest difference I see between myself and others is makeup. At work, I will be the only person wearing any, and I work with mostly women. I work with kids, and they point it out constantly. I tell them that I wear it because I like it and for no other reason.

  27. Anna

    Ha! This is such an amusing and interesting topic and something that I have very little experience with. Live in NYC for a while and you don’t even think about those categories anymore. You just get used to people wearing whatever they want whenever they want. Perhaps certain offices have their dress codes, but I find it hard to imagine that anyone here would really care if someone was overdressed unless it was just totally inappropriate (cocktail dress to the day job at a corporate office).

  28. Lydia

    I am usually more ‘overdressed’, espeically in the summer (warmer) — even if it means wearing jeans with bright red lipstick. My husband and I walk almost everywhere, and when it is cold, I do wear jeans (with a superbright scarf and coat of course), but in summer, I wear skirts all the time, (even for 15 km walks). I have shortened leggings to wear under skirts and dresses to prevent them from flying when those gusts of wind billow them every which way, and to prevent me ‘worrying’ and to be comfortable while I walk. As a result of the shorter leggings, I have not worn a pair of shorts for 14 years, and I love summer now more than I used to, (when I had a terrible time finding shorts that flattered my hourglass figure). I like dressing in my skirts, dresses, and bright colours, but I can also empathize with people who like to be dressed down, or ‘toned’ down. My sister is the complete opposite of me and she likes to blend in with the crowd because she is self conscious about standing out — I think she is more comfortable when she blends in. I try and encourage her to wear what she likes, and when she does, she has equisite and elegant taste. Each to her own, I guess, but I wanted to thank you for a thought provoking post.

    One last thought though — I beleive people — whether dressed up or not — are motivated by comfort (comfort in their clothing, and in themselves). That being said, I am grateful that clothes (dressier clothes, as well as casual), are becoming more comfortable in their fabrications.

  29. Jak

    As a student if I wear jeans and a nice shirt it means that I’m over dressed. I hate seeing all of the sweatpants around me simply because it tells me that you don’t really care about the clothing you’re wearing even though I can tell you spent at least an hour on your hair and makeup. Sweatpants just give off this vibe that jeans don’t.

    When I go to events I typically dress up, in part because I like to and in part because I feel like we should still put some thought into our outfit when giving a presentation or speaking in front of people. I always dress up for job interviews. My first interview, at McDonald’s, I walked in in black dress pants and a button up. In my more recent one I realized that everyone around me were in jeans and tshirts while I was in a skirt and heels. For my generation I think there might be a hard lesson learned when we hit the workforce that you have to present yourself correctly when doing certain things and they just won’t know how.

    Personally, I’ll err on the side of overdressed. It’s just more fun 🙂

  30. Ana

    Oh, I am a terrible over-dresser, to the point where I almost feel incompetent in coming up with casual outfits, but the older I get, the more comfortable I am with it. The occasional back-handed compliment is about the worst I’ve ever got from my over-dressing, and I’m OK with that.

  31. Lauren @ Sassy Molassy

    This was a fun, thought provoking post. I am generally appropriately dressed at work (business casual), but after hours tends to be more jeans and a lululemon zip up for me. I do love rocking my Frye’s and a fun sweater with nice jeans as well on the weekends after I’ve done all my running. As a person who is constantly changing in and out of running clothing, it’s a bit harder to want to dress up simply because my body is seeking comfort and coziness and most of that in my woredrobe lies in casual garb. Even so, I love the opportunity to dress up and own more dresses than someone who rarely wears them should.

  32. Tracey

    I live in Vancouver – the home of Lululemon. I’ve seen people wearing yoga pants to all sorts of inappropriate occassions. I love my yoga pants, but not for a business meeting. My favourite is when people try to dress up their yoga pants. Why not just wearing a nice pair of pants or jeans instead?

    I’m with you, I prefer to be a bit over dressed. I always feel better and more confident when I put on something cute. Even if I’m just going to the play gym with my son.

  33. Leigh

    I love to dress up for work, and wear a skirt and heels most days. But I had a lot of trouble with weekend wear–when I shopped, I only shopped for work stuff, so I never felt like I had anything to wear out running errands on the weekends. I eventually figured out how to mix my less-dressy work clothes (cardigans, flats, etc.) with jeans, and when I throw some accessories in that mix I end up with cute weekend outfits that are still comfortable. I feel so much better when I’m dressed nicely, and going to the grocery store in a statement necklace and swingy cardigan makes it feel less like a chore.

  34. Eliza

    I’m going to a college with a lot of theater students. Many of my classmates dress uniquely in some way, though with varying levels of formality. Guys in everything from a pinstriped suit which SPARKLES, next to another in full hipster uniform, next to a guy all in tweed, oxfords, and a flat cap. The girls are often even more dramatic. The interesting thing about this enviroment is that I only feel like I stand out when I wear my most conservative clothes. I could go to class in a ballgown without anyone taking notice, but anything that would be appropriate office wear immediately stands out. I like this enviroment, but wonder what we all are going to do when we graduate!

  35. hellotampon

    I’m usually overdressed. I don’t wear “classy” expensive clothing, but instead of the jeans and tee shirts (or sweatpants) that everyone else wears around here I go for skirts and dresses with boots or sparkly flats and funky accessories. I feel less insecure about my body when I have something stylish on and just better overall. I started dressing less casually when I took a CNA job. I spend 40 hours a week in scrubs and have no desire to schlep around in sweatpants the rest of the time.

  36. Megan Mae

    I love being overdressed, but it’s not hard to be overdressed in a town of people who do wear sweats, crocs and any number of “slouchy” “comfortable” clothes. Up to and including professors, students, even older ‘church ladies’. I try not to pay too much attention, provided the comfy clothing people wear actually fit – meaning not borderline indecent, which way too many classmates in college have skimmed that line.

    I get a lot of flack for “dressing up” even if I’m wearing a skirt or simple dress, but I’ve learned to mostly ignore it. I wear my own version of comfortable clothing, it just happens to be “dressier” than the average.

    I like dressing up and do miss that some places don’t expect a certain level of dress. Upon visiting a well known art gallery in Nashville, there are signs urging you not to have to dress up to go visit the gallery. I always make an effort to at least wear slacks or something nicer than jeans and tee because I feel like you said – there’s a level of formality that goes into certain events that should be respected.

    • laura

      hahaha Crocks have to be the ultimate in casual wear. I almost forgot about them. my town has some also!

  37. Funnygrrl

    I just wrote about this in a post. I sewed a dress for the ballet and ended up the most dressy one there. I paired it with a knit shrug and boots. I figured I couldn’t be overdressed at THE BALLET. I was wrong.
    But I don’t mind at all. I feel like I’m showing respect to the performers, my date (my husband) and mostly to myself. For me I think how you dress shows how you feel about the situation/person. It is respectful to make some effort if the situation calls for it.
    (I was recently told that I overdressed to do house painting?! The only crummy t-shirt I have has a crocheted neckline….I’m sorry!)

    • Jak

      I don’t understand how you overdress for painting. You basically wear whatever you feel comfortable ruining if you get paint on it…

  38. Trystan (the CorpGoth)

    I am totally one of those ppl who think that casual clothing will bring about the downfall of society! I’m judgy! If I never see PJ pants in public again, I’d die a happy woman 😉 Seriously, I see teenage girls wearing them at the mall & older moms wearing them at the grocery store. Put on some real pants, please.

    The idea that “comfort” can’t be had without wearing saggy fleece is ridiculous. There are plenty of fashionable clothing lines that fit & are made of high quality natural fibers that feel luxurious & don’t look like you should be tucked up in bed. Heck, you can find decent stuff at Target & Old Navy. Some ppl just aren’t trying, they’ve given up, they don’t care about themselves enough, I don’t know what their problems are, but I hate seeing it, ugh.

    That said, I am not a complete overdresser. I have goth friends who won’t set foot out of the house without full makeup, coiffure, & a complete elegant gothic ensemble. I’ll just throw on jeans & a hoodie to get groceries or take the cat to the vet. But for anything else, esp. my super-casual high-tech workplace, I put on heels, lipstick, a coordinated outfit (usually w/a skirt), jewelry, fancy hairdo, the whole deal.

    And, as several ppl noted, certain places / events require appropriate levels of dress. 11 years later, I’m still annoyed that one of my husband’s friends showed up at our very formal daytime wedding in jeans & a polo shirt. Feh! I’ve seen this far too often at weddings & funerals — everyone should own a suit / nice dress for these things. Casual culture strikes again.

  39. Laura

    Great post! Very thoughtful and well-written. I live in a part of Oregon which is famous for its young 20-something girls going everywhere in sweats. Since this style tends to get associated with ALL young people – ie, all young people are currently jobless and lazy and wear sweats all the time – I take great pride in breaking the mold. I wear skirts at least two days a week to work, and my wardrobe is full of cardigans and blazers and cute jewelry, and I will go to Winco wearing eyeliner and my green wool trenchcoat.

    As for the theatre/ballet/opera, I love the excuse to get totally dressed up! That cocktail dress doesn’t get enough use anyway!

  40. jentine

    I think it’s pretty clear where I stand on this topic. I don’t get a lot of chances to wear nice clothes (especially in the growing months when I am working outside so much) so I dress up every moment I get. To me, it’s not just about dressing up or being over dressed, it’s about clothing. I genuinely love clothing (cars, gadgets, electronics…meh) and so dressing up is just fun for me. It’s not the outside pressure that makes me dress up, it’s the joy it brings me within.

  41. L. of Academichic

    Great post! I definitely err on the side of over dresses rather than under dressed. I wrote this fall about how I was “easing” my colleagues into my dressing at first and then was the recipient of comments such as “you’re making the rest of us look bad!” I’m like you in that I just love dressing up. I loved it as a kid and now I love it as an adult – and if my hot pink tights make someone else smile and laugh, I’ll take the smile and laugh as a sign of joy rather than ridicule. I personally feel like dressing up to teach also gives me presence in the classroom and mentally psyches me up, but that’s just me! Thanks for this discussion!

  42. Audi

    I feel FAR more comfortable if I show up overdressed for an occasion than I would if I were under-dressed (although that pretty much never happens). But what’s interesting is that if you really dissect my wardrobe you’ll see lots of jersey knits, jeans, cardigans, chunky boots, and many other items that could never be called formal. The only difference is that I put things together with a lot of thought and intent, and I tend to choose items that are unique and interesting, and for that people often say I’m “dressed up” even though I consider most of what I wear to be on the casual side.

  43. Sarah

    I’m always overdressed. I dress a bit like a 1950s secretary, so people always ask why I’m dressed so nicely, which can be a bit uncomfortable. But I like it, I’m just not comfortable in jeans and t-shirts, I prefer skirts and button-ups.

  44. Amelia

    My favorite Oscar Wilde quote:
    “You can never be overdressed, all other people are under dressed.”

  45. Jenny in NC

    I’m a habitual under-dresser. I could wear jeans and a black t-shirt every day of the week–mostly because I can’t stand to be uncomfortable. Heels hurt my feet, sweaters and layers overheat me, button-blouses bind my broad shoulders, many fabrics irritate my skin. But I try to avoid sloppy. I always wear a bra; no jammies or sweats to the store; etc. I also make a special effort for Sundays. At my church, people traditionally dress up. Dresses and skirts for women, suits and ties for men. My pet peeve is denim skirts and casual sandals at church–even I won’t go that far!

    • STL Mom

      At my old church, teenagers would wear flip-flops — even when they were acolytes! Flop, flop, flop down the aisle…

  46. Carol

    I’m a SAHM and I’ve also lost a lot of weight in the last 3 years (over 100 pounds). When I was very overweight, I wanted to dress better, but never seemed to have the energy for more than jeans/capris and a nice-ish Tee. Now that I’m at a healthy weight, I’m trying to stretch my creative fashion muscle, but I still find myself gravitating towards jeans and a cardi with a tee most days. I wouldn’t say I’m underdressed since I spend my days running errands, driving kids here and there and volunteering, but I definitely always try to dress up a little bit more for meetings and social events.

  47. Anna

    love how you handle this topic sally! i agree with everything you say.

    that said, i’d like to ask all you fancy dressers to go easy on judging those of us in sweats (i know nobody here has been particularly judgmental). i am a post-fancy dresser, pregnant for the first time, and went about four months wearing little but my husband’s sweats because i didn’t fit into any of my old clothes and was unemployed and unable to afford new ones (and maternity clothes are intimidating to say the least!). i am getting back on my feet now (there are some adorable maternity clothes!) but anyone looking at me would probably have thought i was just some slob (my pregnancy is only now becoming obvious at 5.5 months). i love clothes, so it was a dark time! but it helped me see how much we should give people the benefit of the doubt.

    • JB

      I feel for you, Anna! When I developed chronic pelvic pain so many of my clothes were just too uncomfortable to wear, so I went from a “respectable” (if not particularly creative) style to wearing sweats basically all the time. Over time I found skirts and dresses that worked for me, and actually the result was that I developed more of a style than I had before. But every time I see someone in sweats I do try to give them the benefit of the doubt, since I’ve been there.

  48. Emma at Daily Clothes Fix

    I am definitely an over-dresser and feel more comfortable dressed up than dressed down. Last week I was required to wear a t-shirt and jeans to work and one of my lovely male colleagues said he couldn’t work out what was different about me and then he realised that it was that I was dressed down. I thought it was a nice comment and interestingly, I actually felt uncomfortable all day.

  49. rb

    I’m going to guess that a greater percentage of your readers than the general population will cop to being on the overdressed side. Particularly if overdressed is in relation to our increasingly casual society. If you’re into reading style blogs, you’re probably someone who at least thinks about what they look like!

    I am definitely on the overdressed end of the spectrum. My workplace has gone business casual and I have mostly not. I wish it hadn’t gone to business casual, because I think it has changed the overall professionalism of the office – not just in dress but in work product. I would stick out too much if I still wore suits or suiting separates every day, so I save those for external meetings. But I am still “dressy,” while most have gone really more straight casual than business casual is supposed to be.

    I am also somewhat overdressed for weekends in my home city of Berkeley, but again, it would actually be more of a challenge to be underdressed in Berkeley! There has been some negative reaction, but you know what? I’m intelligent and successful, and definitely a feminist, and I don’t need to wear birkenstocks and grow a little mustache to prove it.

  50. The Budget Babe

    Great post. PJ pants in public places make me cringe, as do under-dressers at events like weddings and funerals (show some respect people!).

  51. Penelope

    I’m an overdresser. I went into a rut for the last few years trying to fit in and work (pretend to be normal) but I’ve been recently rediscovering what feels like dressing like the real me.

    When I was in high school and college my friends had a joke about how it wasn’t that I was overdressed, it’s just the rest of you were clearly underdressed for the occasion. I would often go to class and be the only person not wearing jeans as I mostly wore skirts and velvet pants with elastic waists, or the occasional dress.

    Nowadays I always debate what to do when work has its occasional jeans dress-down day. Everyone else clamors for these and acts like its a big reward because their jeans are apparently so much more comfy than what they normally wear to work. I have NEVER found jeans comfy, I can’t find any made to accommodate my thighs (esp. when I still rode horses regularly) that also narrows in enough/is high enough at my waist. I know there are other hourglass shaped women out there who can find jeans, they have to exist, but then you throw in wearing a petite size 00 and it’s like, why even bother trying? (I have a long torso for my height–I actually have to hem most petite pants.) My comfy pants are workout pants (not sweats, more tight-fitting).

    I also just love experimenting with clothing anyway. I am the sort of person who loves all excuses to dress up in beyond-the-ordinary- whether it’s steampunk for a con or something for historical reenactment or a Halloween costume or whatever. I have a quite the wardrobe of “costume pieces” because I keep everything I get for that kind of stuff so I can remix easily. I love being a person who can go into their closet and throw together awesome costuming without buying anything, often half of it from day-to-day pieces with just the right extra bits.

    I just get so bored if I can’t have fun with my clothes. The only exception is the months of January and February- when I’m cold I want warm pants and two shirt layers under a nice warm sweater and some knee-high socks under warm boots and a scarf. I HATE being cold. (I also do layers with skirts for winter, but when it’s really cold and dark out they’re never enough.)

  52. Marsha Calhoun

    Thought-provoking as always – and as a work-at-home person for decades, I have to fight the tendency to dress for immediate comfort only (it helps that my spouse is here to see me, so I have a little more motivation to get out of my bathrobe in the morning). In public, I dress probably more dressily (word?) than others – I hate bare legs with anything but sandals, and one friend’s daughter once asked me what I was wearing on my legs and under my skirt (pantihose/stockings – she had never seen them before). I also put my foot down when asked if my stepson had to wear long pants to my wedding – yes, he did. Weddings and funerals require long pants, I don’t care where they are held (even underwater). Have you noticed how wedding wear and funeral wear are now just about interchangeable? (And on another topic, have you noticed how grown men don’t seem to be willing to leave boyhood behind and put on long pants, shirts with buttons, or socks? We seem to have a world full of 35-year-old toddlers, and I have to fight the impulse to ask them what they were thinking when they got dressed.) Curmudgeonly yours . . .

  53. Nadia

    Being a busy young mom, I’m usually under-under-underdressed. I have been wearing jeans and brownish cardigan over nursing tee for almost a year. Though I’m starting to pick some of my before-pregnancy pretties from the closet. Hmm… maternity does change body, most of my old stuff looks wierd on my current curvies…

  54. Sheila

    I am way more overdressed than the majority of people that I see at work, in public, anywhere. I enjoy being more dressed up – as you said, it denotes my own self-respect and my belief that life is for fun, and what is dressing up, if not fun? I didn’t waste all those hours playing dress-up as a kid!

    BTW, love the BB Dakota leather jacket and am going to steal your sock idea for my perimenopausal pits.

  55. adrienne

    i`d prefer to overdress for an occasion but as a university student under the Environment faculty, it is more of a `trend` to underdress! I`m not talking about your stereotypical hippies (there are some) but if you overdress you`ll probably get a couple of stares. Of course, the `owning it!` factor helps 🙂

  56. Jordan

    I’m with you 100% on this. I am always overdressed it seems. I think part of it is where I live. I live in Florida close to a lot of touristy spots, and most people here dress very casual because of the heat and when people are out touring new places they don’t typically get very dressed up. Its not unusual to see women walking around in nothing but a bikini and flip flops in a grocery store after leaving the beach, and men going shirtless wearing board shorts and nothing else in Target.

    I was very surprised last year though, when I went to a special event when our local symphony orchestra gave a performance. Where I used to live, people got dressed up to see an orchestra play or see an opera, really dressed up. I wore a floor length navy blue satin gown and my husband wore a suit. Back home this would have been totally acceptable attire. The couple we went with was dressed totally different from us. My female friend wore a cute teal sundress and her husband wore jeans and a tee shirt. I was sure that they would seem very casual compared to everyone else at the event. To try to make my friend feel more comfortable, I removed almost all my jewelry in an effort to make my outfit seem less dressy. When we arrived at the event we stuck out so badly! Everyone else was wearing shorts and jeans, the women mostly wore little sundresses. The ones more dressed up wore cocktail dresses. Me and my husband looked ridiculous. People were talking about us and saying catty remarks behind our backs intentionally loud enough to where we could hear them!! The couple acted embarrassed to be seen with us and my husband was mortified. I’d had no idea that events like that around here were so casual. It was awful. I did not own my look that night. Most of the time I do but it was just too hard when hundreds of people were looking at us like we were freaks. When the event was over I pretty much sprinted back to our car. I hadn’t felt like that since high school.

    The way that I was raised was that dressing yourself nicely was a sign of respect. Not just for others, but for yourself. I was taught to dress up nicely when visiting my grandparents or when going to a job interview as a sign of respect for those people. The same for dressing respectfully at a wedding or funeral, or when going to church. At my wedding, my husband’s family deliberately dressed in all black and brown to show their disapproval. In all our wedding pictures you can tell my family from his easily because my side wore bright happy colors and his side looked like somebody died, because everyone was wearing black and nobody smiled. I was taught to never ever try to take attention away from the bride either, and to be as understated as humanly possible. I was also taught never to reveal cleavage or any leg above the knee, or wear anything strapless in church or at a funeral. As a teenager I once wore a white skirt to church, and at home it seemed fine, but the church was so extremely well lit that inside the sanctuary it was see through! Worst of all I was wearing a lavender thong. I was asked never to come back to that church again.

    • rb

      Hi Jordan,
      As a long time sympbony and opera-goer I thought I’d share the following with you, as there really is a dress code for these events and this might make it easer.

      Opening nights – once per year for each group (symphony, opera company, ballet company, etc) are usually “black tie” events and tickets are quite expensive because a huge portion goes to the charity aspect of the organization. This is when women tend to wear floor length gowns and have their photos end up in the paper. There is usually some sort of benefactor party or reception in addition to the performance on that evening.

      Regular performances: The dress code is dressy but not formal. So your husband’s suit would have been fine, and your dress would probably have been fine if it had not been floor length. Yes, the people in jeans and t-shirts were underdressed.

      Special exceptions: Holiday performances. These are still not black tie, but people dress up more than the rest of the year. It would be less unusual to see some taffeta at these events, especially on little girls all dressed up to see The Nutcracker ballet. But again, it probably wouldn’t be floor length on grown up ladies.

      I think the confusion about dress code arises from the newspaper coverage of symphony-goers in their formal dress. Also, it seems when any character in a movie goes to a classical performance, they are dressed for opening night. Some people think all performances have this dress code as a result.

  57. coffeeaddict

    At the risk of everyone coming down on me like a ton of bricks I have to disagree partially with what you said. While I firmly believe in dressing up or down to one’s heart desire and imprinting our own personality in dressing. After all that’s what it’s all about. If we wore clothes only to stay warm, we’d all be sporting overalls in some techno fabric that prevents hypothermia.
    I however disagree on dressing inappropriately for certain events/places. You mentioned opera. I’m sorry but dressing appropriate for such a formal occasion is part of good manners. It doesn’t have to be a full length dress mind you, simple dress pants and a blouse will do. We are still left with plenty of choices to wear something that reflects our sense of style. I believe that by dressing formally to theater /opera, a way of honoring the performers.
    Another one of my ticks involves dressing appropriately for a funeral. I won’t go into detail, because it would take too much time and space. On that note: I would really like it if you did a post on funeral wear one day.
    Happy Friday!

    • Summershoes

      I totally agree what coffeeaddict has said, as I agree with some points in Sally’s original post. I really do think dressing is a matter of one’s personality and therefore a … let’s say, personal matter. And it sure is sometimes about manners and a way showing respect to others. People who go to the theatre or opera in jeans tend to be the same people who answer their mobile phones during plays. And the people who go everywhere in blue jeans — be it a wedding, a funeral or meeting with a royal family.

      And maybe it makes me a bit judgemental, but what’s with the hobo-style hype that has been going on for a few years now?

  58. Redhead Lynn

    In my eyes, I just like to think that my “casual clothing” is more classy than that of most people! Dressing up, to me, is silk and satin and really expensive fabrics…. My casual is a nice blouse with jeans or slacks, or a simple cotton dress in a classic color. So while that does make me overdressed compared to the stretchy-tee crowd, I try to view it as being more “put together” rather than thinking of it as “overdressing” ! But I am with you there. 🙂 Give me overdressed any day! And don’t get me started on men in button-up shirts…. *drool*….

  59. Veronica

    I would prefer to be over-dressed 100 fold over being under-dressed. To me being under-dressed to an event is a sign of disrespect and lack of any thought at all. I’m a SAHM and I LOVE to dress up. My husband’s company had their winter party and the dressing of people went from business casual to black tie. My husband and I and our friends were among the dressier. I loved my dress and i can’t wait to wear it again, sadly that’s probably far off. lol I also wear make-up every day because it makes me feel good and I love to try new colors and I love dark berries or reds on my lips, although I don’t wear them often I love it when I do. I’m also in a bit of a frump with my bottoms though because I’m in the process of trying to lose weight and don’t want to buy too much because it, hopefully, won’t fit for long. So my daily wear involves jeans on most if not all days. I do try to dress up my tops but again I have a 10 month old so it can’t be anything too nice and definitely has to be washable. lol

  60. Meredith

    I believe that looking nice and put-together in public is a form of respect and kindness to others! La bella figura and all that. I’m inclined to laziness rather than primping, and putting on makeup in the morning is a real discipline-builder.

  61. Laura

    This is such an excellent answer! I hate the terms “overdressed” and “underdressed” because clearly the dresser looks like she does for a reason, and who is anyone else to judge her for her reason?

  62. Kalee

    I don’t think I overdress per se. However I tend to “pull myself together” differently than friends. For instance I wear a lot of simple, classic clothes, with black tees being a favorite lately. But I generally add a punch of color with a green houndstooth silk scarf or a statement necklace or a blazer. It’s that little added extra that I don’t think twice about, but has had others remarking on me being more “dressed up.”

  63. glaize cuaresma

    I completely agree that there is no “overdressing” since it’s one’s personality that is involved here.We all have different personalities, different choices, different orientation, different styles so who are they to judge us according to how we look? and besides, everyone has his own personality so IT IS expected that some people would differ in terms of clothes compared to others..